New England Scenic Drives and Historic Sites in 5 Days Itinerary

Enjoy a morning coffee at Eastern Standard Kitchen & Drinks in Kenmore Square. Then, head to Cambridge for a self-guided tour of the prestigious Harvard University and its notable spots like Harvard Square and the Harvard Museum of Natural History.

Have lunch at Giacomo's Ristorante in the North End, known for its Italian cuisine. Post-lunch, visit the innovative Massachusetts Institute of Technology (MIT) and explore the nearby Kendall Square and MIT Museum.

Indulge in a sophisticated dinner at L'Espalier, offering fine French cuisine. Afterward, take a leisurely walk along the Charles River to enjoy the serene evening ambiance.

Start your day with a breakfast sandwich at Neptune Oyster in the North End. Then, take a guided tour of the iconic Boston Fenway Park to learn about its history and significance.

Enjoy a seafood lunch at Row 34 in Fort Point. Afterward, immerse yourself in the art at the Institute of Contemporary Art (ICA) and explore the vibrant Seaport District.

Dine at Oleana, offering a unique blend of Mediterranean and Middle Eastern flavors. Cap off the evening with a delightful stroll through the historic Longfellow House (Washington's Headquarters) and its surrounding neighborhood.

Begin your day with a breakfast at Santarpio's Pizza, a local favorite. Then, immerse yourself in the spooky history of Salem with the Salem Secrets of Salem Hidden History Walking Tour and visit the Salem Witch Trials Memorial.

Enjoy a variety of brews and learn about Salem's haunted past on the Salem Boos and Brews Haunted Pub Crawl. For lunch, stop by Menton for an exquisite French-inspired meal.

Dine at Union Oyster House, America's oldest restaurant, and then continue your exploration with the Salem Night Tour Haunt and History Guided Night Tour to experience the city's eerie atmosphere after dark.

Enjoy a classic American breakfast at Abe & Louie's, known for its steaks and seafood. Then, take a ride on the Boston Hop-on Hop-off Old Town Trolley Tour to get an overview of the city's major attractions.

Have a slice of history with your pizza on the Boston North End Pizza Tour with 3 Slices and Cannoli. Afterward, explore the Isabella Stewart Gardner Museum and its beautiful art collection.

Conclude your trip with a memorable dinner at Craigie on Main, offering a farm-to-table dining experience. Afterward, enjoy a live performance at the Scullers Jazz Club to immerse yourself in Boston's vibrant music scene.